The Post-Purchase Flow is one of the most vital retention flows — but it won’t keep everyone forever.
Some people will fall off. They’ll fail to buy from you again…
Or, if you sell subscription offers, some may cancel their subscription despite your best post-purchase efforts.
You need a Winback Flow (or many, depending on your business model/offers) to “plug” this “leak” in your retention infrastructure.
Check out this guide to The Winback Flow for more information. We’ll discuss how these flows work overall, then highlight some differences in goals, benefits, and best practices for one-off vs. subscription offers.
Understanding the Winback Flow
Defining a “Winback” Opportunity
The definition of a winback opportunity depends on the business model.
For brands with one-off purchase offers, a Winback Flow triggers when a customer goes a certain stretch of time without making a purchase.
For subscription-only brands, Winback Flows trigger when a customer canceled their purchase a specific number of days ago and hasn’t started their subscription again. Subscription brands can implement a similar idea for customers who pause but do not cancel their subscriptions.
Winback Flows can consist of both email and SMS messages.
(NOTE: Winback Flows and Winback Campaigns like this one are different. The former is an automated flow that triggers a set time after canceling/placing the last order. The latter are just broadcast emails that can be sent at any time.)
Goals and Role
Winback Flows aim to either:
- Get more purchases from one-off customers
- Bring back old customers familiar with the brand
In both cases, your goal is to secure repeat business from customers who have bought from you previously.
How the Winback Flow Helps Your Business
The Winback helps your business in several ways:
- Widens profit margins: Repeat business costs less than new business. Lower cost of acquisition. Thus, you can earn a wider profit margin (assuming the same order value/revenue) through cross-selling or securing a resubscription.
- Boosts customer loyalty: Winning customers back can increase customer loyalty, especially if your business has improved (more products, better customer service) since they canceled. You could even turn dissatisfied customers into brand advocates.
- Grabs market share: Your “canceled” customers may be with another brand. Winning them back could “steal” them back from a competitor. Their loss is your gain!
- Makes scaling easier: A lot easier to scale by acquiring the less-expensive “winback” customer. Not only do profit margins widen (see benefit #1)… but onboarding those customers is easier since they’re familiar with your brand. That goes for one-off and subscription brands.
- Improves list health: The customers the Winback Flow targets tend to be less engaged. Thus, this flow can improve list health by re-engaging customers.
- Offers valuable market research: Winback Flows help discover why customers canceled through replies and surveys. You can apply these findings to your copy, offers, website UI/UX, and more.
The Key Components of the Winback Flow
Winback Flow components may vary depending on whether:
- You sell a one-off product/service and are trying to secure repeat business, OR
- You sell a subscription offer and are trying to get canceled customers to resubscribe
Still, there is some overlap. So let’s look at the barebones of a Winback Flow that you can modify for your business model.
Keep in mind that this is just a skeleton. You can add more emails to these, as I’ll discuss later in this section.
One-Off Offers
Reminder Email
The first email reminds the customer of their previous purchase and/or that they haven’t purchased in a while.
Subject Line
If you remind the customer of their last purchase, you should reference it in the subject line. Try something like:
“How’s your [product], [fname]?”
“How’s your purchase treating you?”
“Got any questions about your [product]?”
If you go for more of a “haven’t purchased in a while” angle, you need to subtly address that the customer hasn’t purchased in a while. Your subject line could be something like:
“you alive?”
“you up?”
“It’s been a while”
The latter angle here is the only viable one for subscription brands winning back canceled customers.
Body Copy
If you remind the customer of their last purchase, ask if they’re enjoying it. Maybe offer them a tip to get the most out of it.
If you’re taking the “haven’t purchased in a while” approach, lean more into the humor and personality. For instance, “Haven’t heard from you in a while. Are you still alive?” And you can tailor this to your industry.
For example, if you sell food, you could ask them how they haven’t starved to death without your product.
Or if you sell fitness supplements, ask them how they haven’t srhiveled up into a frail husk of a human (if that fits your brand voice, of course).
(This latter approach, once again, is the only realistic angle you can take if you’re a subscription brand mailing canceled customers).
In either case, follow that up with a “here’s the deal” type of segue and offer them the discount + CTA + urgency.
Conversion Booster Follow-Up Email
This email reminds the customer of their discount with even more urgency.
Subject Line
This is a check-in email, so don’t get fancy. Stick with your gut here. Ideas include:
“Still want this?”
“[Reminder] Discount expiring”
“Checking in”
The point: Conversational and straightforward, with a touch of urgency.
This angle can work for one-off and subscription offers since the focus is the limited-time discount/other compelling offer.
Body Copy
Restate the offer and reiterate the urgency. Consider adding a line or two of benefit-driven copy, but don’t get carried away.
Other Emails
“Discount laddering” is a great approach to Winback Flows I learned from Chris Orzechowski.
This involves sending 1-2 emails with a 24-hour discount…
Then waiting at least several days…
Then sending another 1-2 emails with a bigger discount…
Then waiting at least several days…
Then sending one final set of 1-2 emails with an even bigger discount.
That brings you to a total of 3-6 emails, depending on whether you use a conversion booster email with each main email.
You can get creative with the angles here — as long as they touch on the “come back to our brand” theme.
SMS
SMS’s work well in Winback Flows alongside the emails — particularly as conversion boosters. If you send a conversion booster 12 hours before a discount ladder discount expires, you can send the SMS an hour or so later with a final reminder.
Best Practices For the Winback Flow
Here are some tips and best practices to keep in mind for each piece of the Winback Flow:
Triggers and Filters
For one-off purchases, a customer should enter this flow when they have not purchased in X time (such as number of days).
For subscription offers, a customer should enter this flow X time (such as number of days) after canceling their subscription.
If you sell one-off and subscription offers, you may need to build separate flows (or, at least separate flow branches) for each.
In both cases, consider also adding a “has made a purchase at least once over all time” just to make sure this doesn’t go to people who haven’t bought.
Other flow filters to include are as follows:
- Has not added to cart since starting this flow — Send them to a relevant Abandoned Add to Cart Flow…
AND
- Has not started checkout since starting this flow — Send them to a relevant Abandoned Checkout Flow…
AND
- Has not placed an order since starting the flow — If they buy, this flow is no longer relevant.
AND
- Has not been in the flow within X days — We don’t want to hit customers with this constantly. They’ll get annoyed and feel like you see them only as $$$. For example, filter out anyone who was in this flow in the last 30 days.
AND
- Is not suppressed for email
AND
- Is not DNC (for SMS)
Lastly:
If you have the data, create splits in your flow based on cancellation reason (cost, dissatisfaction with customer service, etc.). This lets you build more targeted messaging around why the customer canceled… increasing conversion rates.
This will involve building a cancelation survey or sending a one-click “cancelation reason” email.
Time Delay
The time between the last purchase/cancellation and this flow should be long. You want to win back the customer, yes, but you do not want to bombard them with “come back!” emails.
For one-off offers, 30 days is a good place to start. If you’re doing email right, you’ll have a Post-Purchase Flow and mail your list regularly. Customers will have plenty of chances to buy again.
For subscription offers, you can experiment with shorter times between cancelation and Winback Flow sends. I wouldn’t go shorter than two weeks (this gives them enough time to “cool off” and “forget”), but hey, feel free to test things.
Time delays between each email can vary widely. If you take a “discount ladder” approach, space out each email by the same amount of time as the triggering time delay. If you use “conversion booster” emails, send these 12 hours after the regular email.
If you aren’t taking the discount ladder approach, keep emails 1-2 days apart.
Copy
The copy should have plenty of brand-fitting personality and a brand-appropriate level of humor. Something to be said about “making customers laugh as they pull out their credit cards to buy again.”
Still, don’t sacrifice the sale at the altar of wit. Keep it clear and concise. Especially for any conversion booster emails.
This excludes any emails that use story to win the customer back — these emails may need some more copy to flesh out the story. For instance, an email discussing how “John Doe in the fulfillment center’s been sad ever since the customer canceled their order/stopped buying.”
Design
Winback emails should not have many or any design elements. A logo, signature block, and funny image/gif (if it fits the context) at most.
Remember: These customers are less likely to open and buy. You can’t get away with all that HTML. It looks too salesy and can harm deliverability on a flow that inherently won’t perform as well as others.
Measuring Success for the Winback Flow
Here are some key metrics to track for the Winback Flow and how to improve them:
Click-Through Rate (CTR)
Winback Flows may get high opens when timed right. However, getting the customer to actually click to the website can be tough in some cases — particularly for subscription companies targeting canceled customers.
Thus, this is one of the most vital KPIs alongside conversion rate.
How to improve:
- A/B test CTAs (and make sure they’re clear, concise, and prominent).
- A/B test CTA placement.
- Segment subscribers and personalize content.
Conversion Rate
People might click through at a higher rate but not buy. This could potentially indicate confusion on your site, or that you’re not building enough value in the email.
How to improve:
- A/B test copy.
- A/B test offers, promotions, and pricing strategies.
- Use incentives + urgency.
- Optimize your website/online store.
Average Order Value
The key to sustainable scaling is maximizing customer retention… and that means increasing your back-end revenue. Thus, the higher the AOV on the winback purchase, the better.
How to improve:
- A/B test offers, promotions, and pricing strategies.
- A/B test offer structure, such as bundles and offer names.
- A/B test copy.
- Segment your audience by purchase history and behavior to offer more relevant product recommendations.
Unsubscribe Rate
Winback Flows for subscription-only brands will likely have a higher unsubscribe rate than regular campaigns and certain flows. After all, you are targeting people who actively canceled their subscriptions.
One-off customers may not unsubscribe at the same rate, but it’s still worth tracking on Winback Flows.
How to improve:
- Test email frequency, timing, and preferences.
- Improve segmentation to deliver more relevant content + offers.
- Honor unsubscribe requests promptly to maintain a positive sender reputation.
Winback Pitfalls to Avoid
Watch out for these mistakes when crafting your Winback Flow:
Poor Timing
Sending your Winback Flow too soon makes you look impatient or even desperate. It also doesn’t give enough time to maximize a customer’s surprise/curiosity when the flow triggers.
At the same time, waiting too long can cause your customer to find another brand and become loyal to that brand.
Same thing applies in between emails and SMS’s. You must find a balance between too long and too short.
Lacking Segmentation
Subscription Offers
Customers cancel for all manner of reasons. Generic Winback Flows are better than nothing, but you won’t achieve the best results unless you segment by cancellation reason.
For example, you run a subscription-only offer. Say a customer selects “cost” (or however you word it) for why they canceled their subscription. Your winback could:
- Discuss why not having your offer is costing your customer more
- Downsell lower-priced items based on their needs
- Show them options for pausing or extending their next purchase date
- Illustrate other subscriptions that meet their needs better.
One-Off Offers
Segmentation’s vital for one-off purchases, too. It helps you upsell and cross-sell the “next logical product” in a customer’s journey.
For example, you sell sleeping/bedding products like pillows, blankets, sheets, etc. Your customer buys a weighted blanket but doesn’t make another purchase for 30 days.
Duvet covers help keep dirt and whatnot away from the blanket (which can be a pain to clean).
That’s a perfect winback cross-sell offer.
Failing to Address Engagement
Customers may reply with feedback, concerns, and questions. Failing to address these promptly can lose the customer for good — they may feel like just another dollar sign if you aren’t showing that you’re here to help.
Failing to Use Incentives Correctly
Customers who don’t buy from your post-purchase flow or broadcast emails have bypassed many non-discounted emails. They may buy from the winback email without a discount, but the prospects are lower.
Therefore, consider a discount… but make it a tight deadline. 24 hours maximum if you take the “discount ladder” approach.
This all presupposes a solid email marketing calendar and your other flows. Without those, your customer doesn’t have those buying opportunities.
The Bottom Line on Winback Flows
The Winback Flow:
- Secures repeat one-off purchases from customers who haven’t bought in a while
- Recovers customers who canceled subscriptions, growing your recurring revenue
Both of these drive your revenues up and acquisition costs down… which means wider margins… which means more money to play with. They can even turn unhappy former customers into brand advocates!
You can start with a simple Winback Flow of 2-3 emails, but experiment with discount laddering, segmentation/personalization, and more to capture more sales.
I’ll leave you with this:
Winback flows are great, but…
They should not be huge money-makers, relatively speaking. If yours is raking in a lot of cash, you have a retention problem. People are dropping off.
Put a minimum viable Winback Flow in place, then fix the retention problem…
And then go back and optimize the flow.
What to Do Next
- Implement this flow into your business if you don’t have it/Optimize your flow with insights from this post if you DO have it.
- Get on my email list using the signup form below.
- Share this post with someone who would find it helpful or insightful.
- Work with me if you want to earn more revenue, widen your margins, and improve retention through email and SMS… so you can quit worrying about acquisition.